EP2247642B1 - Antifouling-zusammensetzung - Google Patents
Antifouling-zusammensetzung Download PDFInfo
- Publication number
- EP2247642B1 EP2247642B1 EP09710494.7A EP09710494A EP2247642B1 EP 2247642 B1 EP2247642 B1 EP 2247642B1 EP 09710494 A EP09710494 A EP 09710494A EP 2247642 B1 EP2247642 B1 EP 2247642B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- coating composition
- antifouling coating
- acid
- polyoxalate
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000003373 anti-fouling effect Effects 0.000 title claims description 93
- 239000000203 mixture Substances 0.000 title claims description 38
- 239000008199 coating composition Substances 0.000 claims description 69
- -1 aromatic diols Chemical class 0.000 claims description 54
- 238000000576 coating method Methods 0.000 claims description 52
- 150000002009 diols Chemical class 0.000 claims description 49
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 46
- 239000011248 coating agent Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000011230 binding agent Substances 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 25
- 239000012855 volatile organic compound Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
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- 239000008096 xylene Substances 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 12
- 235000006408 oxalic acid Nutrition 0.000 claims description 12
- 238000006068 polycondensation reaction Methods 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 239000000049 pigment Substances 0.000 claims description 8
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- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 53
- 238000005498 polishing Methods 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- 238000000034 method Methods 0.000 description 16
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- 125000004432 carbon atom Chemical group C* 0.000 description 15
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 14
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 13
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- 229910052757 nitrogen Inorganic materials 0.000 description 9
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- 125000001931 aliphatic group Chemical group 0.000 description 8
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- 125000005907 alkyl ester group Chemical group 0.000 description 7
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- 230000015572 biosynthetic process Effects 0.000 description 7
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- 230000015556 catabolic process Effects 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
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- 150000007513 acids Chemical class 0.000 description 5
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- 150000001408 amides Chemical class 0.000 description 5
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- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 239000003139 biocide Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 4
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 4
- 229940112669 cuprous oxide Drugs 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000003628 erosive effect Effects 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
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- 238000010438 heat treatment Methods 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
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- 238000002156 mixing Methods 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- 238000013270 controlled release Methods 0.000 description 3
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- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- WJSXSXUHWBSPEP-UHFFFAOYSA-N pyridine;triphenylborane Chemical compound C1=CC=NC=C1.C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 WJSXSXUHWBSPEP-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- WWSBQOYADFGDQE-UHFFFAOYSA-N tridecanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCCCCCC(=O)OC WWSBQOYADFGDQE-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- TUQLLQQWSNWKCF-UHFFFAOYSA-N trimethoxymethylsilane Chemical compound COC([SiH3])(OC)OC TUQLLQQWSNWKCF-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- ZMCWFMOZBTXGKI-UHFFFAOYSA-N tritert-butyl borate Chemical compound CC(C)(C)OB(OC(C)(C)C)OC(C)(C)C ZMCWFMOZBTXGKI-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- MXODCLTZTIFYDV-UHFFFAOYSA-L zinc;1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Zn+2].C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O.C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O MXODCLTZTIFYDV-UHFFFAOYSA-L 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1637—Macromolecular compounds
- C09D5/165—Macromolecular compounds containing hydrolysable groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/015—Biocides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0058—Biocides
Definitions
- the present invention relates to the use of polyoxalates as binders for antifouling coating compositions and to antifouling coating compositions comprising such binders.
- paints are used. These paints generally comprise a film-forming binder, together with different components such as pigments, fillers, solvents and biologically active substances.
- the most successful antifouling coating system on the market until 2003 was a tributyltin (TBT) self-polishing copolymer system.
- the binder system for these antifouling coatings was a linear acrylic copolymer with tributyltin pendant groups.
- the remaining acrylic copolymer, now containing carboxylic acid groups, became sufficiently soluble or dispersible in seawater to be washed out or eroded away from the coating surface.
- This self-polishing effect provided a controlled release of the biologically active compounds in the coating resulting in the excellent antifouling efficiency and smooth surfaces and hence reduced frictional resistance.
- the above mentioned antifouling coating systems degrade by hydrolysis of pendant groups on the polymer backbone, which results in a water erodable polymer.
- the hydrolysis of the pendant groups on the polymer backbone results in the formation of carboxylic acid salts which make the polymer hydrophilic and thereby erodable.
- a certain amount of hydrolysable groups are needed to get sufficient hydrophilicity and an erodable polymer after hydrolysis.
- One disadvantage of this technology is that the molecular weight of the polymer influences the erosion rate and high molecular weight polymers will have lower erosion rate due to entanglement of the polymer chains. Also, silyl ester copolymer technology is expensive.
- Another way of obtaining water erodable polymers is by introducing hydrolysable groups in the polymer backbone, resulting in degradation of the polymer structure, which give erosion of the polymer film or coating film.
- Polyanhydrides are a class of polymers that degrade by backbone hydrolysis. The polyanhydrides are well documented for their surface degradation properties. Surface degradation is one of the most important factors for obtaining a successful antifouling coating.
- the use of specific aromatic polyanhydrides as binders in antifouling coating compositions is, for example, described in WO 2004/096927 .
- the anhydride group is extremely labile in the presence of moisture and it is therefore difficult to design a coating system based on polyanhydrides that exhibits a slow, controlled hydrolysis for use in antifouling coatings. Accordingly, the polyanhydrides used for antifouling coating compositions generally have a high content of aromatic units in order to control the hydrolysis.
- polyoxalates are a class of polymers that are suitable for use as binders in antifouling coatings. Coating films formed using polyoxalates exhibit the necessary surface degradation by degradation of the polymer backbone in the polyoxalate. Backbone hydrolysis in these compounds is more controlled than for the polyanhydrides. Because of the two adjacent carbonyl groups in the oxalate unit, the ester group is activated and labile towards hydrolysis. Polyoxalates have better solubility in common organic solvents than anhydrides and give more flexible coating films than the aromatic polyanhydrides employed in antifouling coating compositions.
- any anti-fouling coating has a VOC content of less than 400 g/L. This is more easily achieved with polyoxalate binder than with the binder system based on silyl copolymers.
- Polyoxalates are not new compounds.
- various polyoxalates are mentioned as being suitable for the formation of shaped articles or films.
- Many other documents describe the formation of various polyoxalates but no-one before has appreciated the utility of these compounds as self-polishing binders in anti-fouling coating compositions for marine based articles.
- the object of the present invention is to provide an antifouling coating composition which can be applied by common application methods, e.g. by painting or spraying the coating composition onto the surface in question.
- the invention also provides antifouling coating films with good mechanical properties, controlled self-polishing properties and good antifouling performance. These objectives are attained by the use of polyoxalates as the binder in the anti-fouling coating composition.
- the invention provides the use of at least one polyoxalate as a binder in an antifouling coating composition, wherein said antifouling coating composition comprises a biologically active agent that prevents the settlement of marine organisms on a surface and/or encourages the dislodgement of marine organisms from a surface.
- an antifouling coating composition comprising at least one polyoxalate and at least one biologically active agent that prevents the settlement of marine organisms on a surface and/or encourages the dislodgement of marine organisms from a surface.
- the invention provides an object coated with an anti-fouling coating composition as hereinbefore defined.
- binder is a term of this art.
- the binder is the actual film forming component of an anti-fouling composition.
- the binder imparts adhesion and binds the components of the composition together.
- the at least one polyoxalate which is used in the invention may be a linear or branched polymer. It is preferably a copolymer, e.g. a random copolymer or block copolymer.
- the repeating units of the polyoxalate can be saturated and/or unsaturated aliphatic and/or cycloaliphatic units and/or aromatic units. The repeating units can be unsubstituted or substituted. It will be appreciated that any polyoxalate of the invention comprises at least two oxalate units, preferably at least 5 oxalate units, e.g. at least 8 oxalate units.
- the polyoxalate of the invention will preferably be formed from the polymerisation of at least one oxalate monomer and at least one diol monomer.
- the polyoxalates of the present invention can be prepared by condensation polymerisation using any of various methods known and used in the art. Examples of common polycondensation reactions include direct esterification reaction between oxalic acid and diols; transesterification reaction between dialkyl oxalates and diols; reaction in solution between oxalyl chloride with diols; and interfacial condensation reaction between oxalyl chloride and diols or alkali salts of diols or between alkali salts of oxalic acid, such as sodium oxalate or potassium oxalate, and diols.
- the polycondensation reactions can be carried out as melt or in solution.
- the polymerisation can be performed under melt polycondensation condition or in solution.
- the polycondensation is carried out in the presence of a catalyst.
- the catalyst preferably comprises at least one member selected from compounds of magnesium, calcium, titanium, zirconium, vanadium, manganese, iron, cobalt, zinc, aluminium, germanium, tin, phosphorus and antimony.
- the compounds organometallic compounds are preferred, more preferably organic titanium compounds and organic tin compounds.
- organic titanium compounds include titanium alkoxides, such as triisopropyl titanate, titanium tetraisopropoxide, titanium glycolates, titanium butoxide, hexyleneglycol titanate and tetraisooctyl titanate.
- organic tin compounds include tin 2-ethylhexanoate, dibutyltin dilaurate, monobutyltin tris(2-ethylhexanoate), dibutyltin oxide, dioctyltin oxide and monobutyltin oxide.
- the starting materials for the preparation of polyoxalates depend on the polymerisation process as indicated in the above mentioned polymerisation processes.
- the polyoxalates are however formed from oxalic acid or a derivative thereof, i.e. an oxalate monomer.
- derivative thereof is meant a mono or diester thereof, a mono or diacid halide (e.g. chloride) thereof, or salt thereof, e.g. alkali metal salt thereof.
- any derivative is one of the oxalic compounds mentioned below.
- the oxalate monomer used in the polymerisation reaction may be an ester of oxalic acid, especially a diester.
- Esters may be alkyl esters, alkenyl esters or aryl esters.
- suitable dialkyl oxalates for the preparation of polyoxalates include dimethyl oxalate, diethyl oxalate, dipropyl oxalate and dibutyl oxalate.
- any alkyl group may have 1-10 carbon atoms, preferably 1 to 6 carbon atoms.
- Any alkenyl group may have 2-10 carbon atoms, preferably 2 to 6 carbon atoms.
- Any aryl group may have 6-20 carbon atoms, preferably 6 to 10 carbon atoms.
- Any cyclic group may have 3-20 carbon atoms, preferably 4-15 carbon atoms especially 5 to 10 carbon atoms.
- Dialkyl oxalates are preferred.
- oxalate monomers are oxalic acid, oxalyl chloride, and salts of oxalic acid, e.g. alkali metal salts thereof, such as sodium oxalate or potassium oxalate.
- a mixture of oxalate monomers to be used in the preparation of the polyoxalates used in the invention.
- the use of two dialkyl oxalates is preferred.
- only one oxalate monomer is used in the polymerisation reaction.
- diols for the preparation of polyoxalates include saturated aliphatic and saturated cycloaliphatic diols, unsaturated aliphatic diols or aromatic diols. Linear or branched saturated aliphatic diols are preferred.
- Preferred diols include C 3-20 aliphatic or C 4-20 -cycloaliphatic diols such as 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 2,4-pentanediol, 1,2-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 2,5-hexanediol, 1,7-heptanediol, 1,2-octanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,2-dodecanediol, 1,12-do
- diols 2-butyl-2-ethyl-1,3-propanediol, 2,2,4-trimethyl-1,3-pentanediol, 4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, and neopentyl glycol and mixtures thereof.
- At least one diol used to manufacture the polyoxalates of the invention is a saturated aliphatic branched diol having up to 20 carbon atoms, e.g. 5-15 carbon atoms.
- a branched diol is employed this preferably forms at least 50 wt% of the diol component used in the polymerisation reaction.
- Preferred unsaturated aliphatic diols are C4-20 unsaturated aliphatic diols such as 2-butene-1,4-diol, 3-butene-1,2-diol, 3-hexene-1,6-diol and monoolein.
- Preferred aromatic diols are C6-20 aromatic diols such as hydroquinone, methylhydroquinone, resorcinol, 2-methylresorcinol, pyrocatechol, 1,2-benzenedimethanol, 1,3-benzenedimethanol, 1,4-benzenedimethanol, bisphenol A, bisphenol E, bisphenol F, bisphenol M, bisphenol P, bisphenol S, bisphenol Z, bisphenol AF, bisphenol AP, 4,4'-dihydroxybenzophenone, 4,4'-biphenol, 2,2'-biphenol, 1,2-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, and 1,8-naphthalenedimethanol;
- diols can be used alone or in combination of two or more diols.
- a mixture of two or more diols is used to manufacture the polyoxalates of the invention.
- the starting materials for the preparation of the polyoxalates are preferably used in a molar ratio between the oxalic acid or derivative(s) thereof and the diol(s) of less than 2 and more than 0.5, more preferred not above 1.0.
- the diols are in excess.
- the oxalate monomers will be in excess.
- the polyoxalates are prepared from aliphatic or cycloaliphatic diols.
- Aliphatic or cycloaliphatic diols preferably form therefore at least 50 mol%, preferably at least 75 mol%, optionally 100 mol% of the total diols used to form the polyoxalate.
- the amount of aromatic diols should preferably be 50 mol% or less of the total amount of diols, more preferably less than 25 mol% or less and most preferably 10 mol% or less.
- the amount of unsaturated aliphatic diols should preferably be 10 mol% or less of the total amount of diols.
- the polyoxalate polymer architecture will influence the polymer properties.
- Branching in polymers and "star" shaped polymers are examples of useful structural variables that can be used advantageously to modify polymer properties such as solubility in organic solvents, miscibility in polymer blends and mechanical properties.
- the polycondensation is carried out in the presence of a compound with more than two functional groups, e.g. three functional groups that can take part in the polymerisation reaction.
- suitable compounds include polyols , e.g.
- C3-20 polyols such as glycerol, trimethylolmethane, trimethylolethane, trimethylolpropane, 1,2,4-butanetriol, 1,2,6-hexanetriol, erythritol, pentaerythritol, di(trimethylolpropane) 1,2,7,8-octanetetrol triglycerol, dipentaerythritol, pyrogallol and phloroglucinol; polycarboxylic acids, e.g.
- C4-20 polycarboxylic acids such as trimellitic acid, trimesic acid and pyromellitic acid; alkyl esters of polycarboxylic acid such as trimethyl trimellitate; and anhydrides of polycarboxylic acid such as trimellitic anhydride and pyromellitic dianhydride.
- poly is used in relation to these branching monomers to mean the presence of 3 or more functional groups (i.e. acid groups, hydroxyl groups etc) in the molecule. These groups therefore allow the formation of a polymeric side chain off the polymer backbone.
- Examples of other suitable polyfunctional compounds include malic acid, tartaric acid and citric acid.
- Polyols with more than two hydroxyl groups are the preferred compounds for obtaining branched and star-shaped polyoxalates.
- the amount of any branching reactant, e.g. polyol should preferably be 10 mol% or less of the total amount of that reactant type, e.g. of the diols/polyols combined. Too much branching leads to gelling and a composition which cannot be applied to an object.
- bifunctional compounds can be included as comonomers to adjust the polymer properties of the polyoxalates.
- Such compounds can be used to adjust parameters such as hydrolysis rate and mechanical properties.
- These functional compounds preferably possess two reactive functional groups e.g. two ester, acid, amino or hydroxyl groups or mixtures thereof and will be called bifunctional compounds. These compounds can form additional monomers in the polymerisation process. Examples of suitable bifunctional compounds include:
- Any alkyl ester of dicarboxylic acid, dicarboxylic acid anhydrides, diamines, hydroxyl functional carboxylic acid, alkyl ester of hydroxyl functional carboxylic acid or dicarboxylic acid used herein may have up to 20 carbon atoms.
- a particularly preferred combination of use in the manufacture of polyoxalates used in the invention is that of an oxalate monomer and a bifunctional compound as hereinbefore defined.
- bifunctional compound will contain at least one carboxylic acid group or ester thereof, preferably two carboxylic acid groups or esters thereof.
- An especially preferred reactant combination is therefore an oxalate monomer and an alkyl ester of dicarboxylic acid, dicarboxylic acid anhydride or dicarboxylic acid.
- Polyoxalate copolymers are obtained by mixing all starting materials before polymerisation. By mixing all reactants, the polyoxalate which forms is typically a statistical random polymer of all the monomers used (i.e. the amount of each monomer incorporated essentially reflects the amount of each monomer in the starting mixture). Polyoxalate block polymers are obtained either by subsequent addition of starting materials during the polymerisation process after an initial polymerisation of only two monomers or preparation of block polymers that are linked together.
- the polymerisation conditions can be widely varied although typically temperatures of 100 to 250°C are employed, e.g. 150 to 220°C.
- a condensate normally water or an alcohol
- This is preferably removed by distillation during as the polymerisation continues. This can be achieved under reduced pressure.
- the polymerisation is preferable carried out in an inert atmosphere, e.g. nitrogen.
- the polyoxalates used in the present invention preferably have a number average molecular weight (Mn) from 1,000 to 100,000 more preferably 1000 to 40,000, especially 1000 to 10,000.
- the polyoxalates used in the present invention preferably have a weight average molecular weight (Mw) from 1,000 to 200,000, e.g. from 1,000 to 100,000 more preferably 1000 to 40,000, especially 1000 to 25000.
- Mw weight average molecular weight
- the Mw may be 10,000 to 40,000, e.g. 20,000 to 40,000.
- the Mw should preferably be 20,000 - 40,000. This ensures the formation of good film properties and maintains an acceptable solubility.
- the Mw should preferably be 1,000- 10,000.
- the polyoxalate is amorphous.
- amorphous is meant that the polyoxalate does not have a discernable melting point, i.e. it is not crystalline.
- the use of an amorphous polyoxalate increases solubility in the organic solvent typically used in the anti-fouling composition so the use of amorphous polyoxalates is preferred. It is remarkable however that such amorphous polymers can be used successfully as self-polishing binders in anti-fouling coating compositions.
- the polyoxalate is obtainable by the condensation polymerisation of at least one oxalic acid or derivative thereof and at least two diols wherein at least one of said diols is a saturated branched diol having up to 20 carbon atoms.
- At least two saturated branched diols are used or a mixture of a linear or cyclic saturated diol and a saturated branched diol.
- Any diol may have up to 20 carbon atoms, e.g. up to 10 carbon atoms. Preferred diols are listed above.
- the at least one polyoxalate acts as a binder in a physical drying antifouling coating composition, i.e. antifouling coating compositions which are dried by evaporation of volatile components, such as solvents. These compositions are typically free of curing agents.
- a physical drying coating the solubility of the binder is important.
- the polyoxalate of such a coating composition has to be highly soluble in the organic solvent used in order to allow formation of a coating composition with a suitable solids content and suitable properties for application by common methods.
- any polyoxalate used in this invention has a solubility of at least 50 wt% in the solvent used in the antifouling composition, preferably at least 75 wt% in the solvent such as at least 95 wt% in the solvent. For example therefore at least 1 kg of polyoxalate should dissolve in 1 kg of solvent.
- solvents are discussed below.
- Xylene is especially preferred.
- the at least one polyoxalate forms at least 3 wt%, e.g. at least 5 wt%, perhaps at least 10 wt% of the anti-fouling coating composition.
- level of polyoxalate binder employed will depend on the amount of anti-fouling compound employed, e.g. the amount of cuprous oxide.
- the solubility of the polyoxalates can, for example, be improved by using flexible building blocks and/or by branching of the polymer by using multifunctional building blocks, in particular the bifunctional building blocks as discussed above.
- the present invention relates to the use of polyoxalates as binders in curable antifouling coating compositions.
- Polyoxalates have functional end groups that are reactive with curing agents such as chain extenders or crosslinkers.
- the resulting cured coating film will generally have improved hydrolysis and mechanical properties.
- Curable coatings are often used to provide an antifouling coating composition with reduced levels of volatile organic compounds (VOC) and sufficiently low viscosity in order to be applied by common application methods.
- VOC volatile organic compounds
- end-groups will depend on the starting materials, the ratio between the starting materials and the process for preparation.
- the end groups can easily be modified to other functional groups suitable for a wide range of curing reactions.
- curable end groups include hydroxyl groups, ethylenically unsaturated groups and epoxy groups.
- Polyoxalates especially those prepared with excess of diols in the polycondensation reaction, can have hydroxyl end-groups. These end-groups are reactive with curing agents such as monomeric isocyanates, polymeric isocyanates and isocyanate prepolymers.
- Epoxy groups may be introduced, for example, by reacting hydroxyl groups in the polyoxalate with epichlorohydrin.
- Ethylenically unsaturated groups such as (meth)acrylate groups may be introduced, for example, by reacting the hydroxyl groups in the polyoxalate with ethylenically unsaturated carboxylic acids, such as acrylic acid or methacrylic acid.
- polyoxalate is used herein therefore to cover compounds which either inherently contain curable end groups or are modified to contain curable end groups.
- Compounds which have been modified to contain curable end groups may be referred to specifically as end group modified polyoxalates.
- the coating composition of the invention can be supplied as a multipack (preferably two pack) formulation.
- kit comprising (I) an anti-fouling coating composition comprising at least one polyoxalate and at least one biologically active agent that prevents the settlement of marine organisms on a surface and/or encourages the dislodgement of marine organisms from a surface (II) at least one curing agent.
- the invention provides a self-polishing anti-fouling coating composition as hereinbefore defined which is curable or which has been cured.
- self-polishing coating is a term of the art and used herein to mean an erodable and hydrolysable coating.
- the curable antifouling coating compositions can be a one pack system, it is preferably a multi pack system. It would be supplied with instructions on mixing the components shortly before application.
- the anti-fouling coating composition is supplied free of any curing agent. During application and once applied however, it is preferred if the anti-fouling coating composition includes a curing agent.
- the antifouling coating composition of the invention should preferably have solids content above 45 wt%, e.g. above 50 % by weight, such as above 55 wt%, preferaby above 60 wt%.
- the antifouling coating composition should have a content of volatile organic compounds (VOC) below 400 g/L, e.g. below 390 g/L.
- VOC volatile organic compounds
- the VOC content can be measured on an anti-fouling coating having a curing agent added thereto or without such a curing agent. Where a curing agent is used, it is preferred if the VOC content of the mixture incorporating the curing agent is less than 400 g/L, more preferably less than 375 g/L, especially less than 350 g/L.
- VOC content can be calculated (ASTM D5201-01) or measured, preferably measured.
- the polyoxalates of the present invention will degrade in sea water and release compounds with structural units similar or identical to the starting materials.
- Starting materials which are biologically active towards marine organisms may give polyoxalates which act as anti-fouling agents themselves.
- the starting materials are chosen from compounds that give polyoxalates that degrade to components that are not biologically active towards marine organisms.
- the antifouling coating composition of the present invention comprises a biologically active polyoxalate, it additionally contains one or more biologically active agents.
- biologically active agent/compound any chemical compound that prevents the settlement of marine organisms on a surface, and/or prevents the growth of marine organisms on a surface and/or encourages the dislodgement of marine organisms from a surface.
- inorganic biologically active compounds include copper and copper compounds such as copper oxides, e.g. cuprous oxide and cupric oxide; copper alloys, e.g. copper-nickel alloys; copper salts, e.g. copper thiocyanate, copper sulphide; and barium metaborate.
- organometallic biologically active compounds include zinc pyrithione; organocopper compounds such as copper pyrithione, copper acetate, copper naphthenate, oxine copper, copper nonylphenolsulfonate, copper bis(ethylenediamine)bis(dodecylbenzensulfonate) and copper bis(pentachlorophenolate); dithiocarbamate compounds such as zinc bis(dimethyldithiocarbamate), zinc ethylenebis(dithiocarbamate), manganese ethylenebis(dithiocarbamate) and manganese ethylene bis(dithiocarbamate) complexed with zinc salt;
- organocopper compounds such as copper pyrithione, copper acetate, copper naphthenate, oxine copper, copper nonylphenolsulfonate, copper bis(ethylenediamine)bis(dodecylbenzensulfonate) and copper bis(pentachlorophenolate
- organic biologically active compounds include heterocyclic compounds such as 2-( tert -butylamino)-4-(cyclopropylamino)-6-(methylthio)-1,3,5-triazine, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, 2-(thiocyanatomethylthio)-1,3-benzothiazole and 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine; urea derivatives such as 3-(3,4-dichlorophenyl)-1,1-dimethylurea; amides and imides of carboxylic acids, sulphonic acids and sulphenic acids such as N -(dichlorofluoromethylthio)phthalimide, N- dichlorofluoromethylthio- N , N' -dimethyl- N -phenylsulfamide, N -dich
- biologically active agents may be tetraalkylphosphonium halogenides, guanidine derivatives, imidazole containing compounds such as medetomidine and derivatives and enzymes such as oxidase, proteolytically, hemicellulolytically, cellulolytically, lipolytically and amylolytically active enzymes.
- the biologically active compounds may be encapsulated or adsorbed on an inert carrier or bonded to other materials for controlled release.
- the biologically active compounds may be used alone or in mixtures.
- the use of these biologically active agents is known in anti-fouling coatings and their use would be familiar to the skilled man.
- the total amount of biologically active agent in the antifouling compositions of the invention may be in the range 0.5 to 80 wt%, such as 1 to 70 wt%. It will be appreciated that the amount of this component will vary depending on the end use and the biologically active compound used.
- the antifouling coating composition according to the present invention optionally comprise one or more components selected among other binders, pigments, extenders and fillers, dehydrating agents and drying agents, additives, solvents and thinners.
- An additional binder can be used to adjust the self-polishing properties and the mechanical properties of the antifouling coating film.
- binders that can be used in addition to the polyoxalate in the antifouling coating composition according to the present invention include rosin materials such as wood rosin, tall oil rosin and gum rosin;
- rosin derivatives such as hydrogenated and partially hydrogenated rosin, disproportionated rosin, dimerised rosin, polymerised rosin, maleic acid esters, fumaric acid esters and other esters of rosin and hydrogenated rosin, copper resinate, zinc resinate, calcium resinate, magnesium resinate and other metal resinates of rosin and polymerised rosin and others as described in WO 97/44401 ; resin acids and derivatives thereof such as copal resin and sandarach resin; other carboxylic acid containing compounds such as abietic acid, neoabietic acid, dehydroabietic acid, dihydroabietic acid, tetrahydroabietic acid, secodehydroabietic acid, pimaric acid, paramatrinic acid, isoprimaric acid, levoprimaric acid, agathenedicarboxylic acid, sandaracopimalic acid, lauric acid, stearic acid, isostearic acid, oleic acid
- Dehydrating agents and drying agents contribute to the storage stability of the antifouling coating composition by removing moisture introduced from raw materials, such as pigments and solvents, or water formed by reaction between carboxylic acid compounds and bivalent and trivalent metal compounds in the antifouling coating composition.
- the dehydrating agents and drying agents that may be used in the antifouling coating composition according to the present invention include organic and inorganic compounds.
- dehydrating agents and drying agents include anhydrous calcium sulphate, anhydrous magnesium sulphate, anhydrous sodium sulphate, anhydrous zinc sulphate, molecular sieves and zeolites; orthoesters such as trimethyl orthoformate, triethyl orthoformate, tripropyl orthoformate, triisopropyl orthoformate, tributyl orthoformate, trimethyl orthoacetate and triethyl orthoacetate; ketals; acetals; enolethers; orthoborates such as trimethyl borate, triethyl borate, tripropyl borate, triisopropyl borate, tributyl borate and tri- tert -butyl borate; silicates such as trimethoxymethyl silane, tetraethyl silicate and ethyl polysilicate; and isocyanates, such as p-toluenesulfonyl isocyanate.
- the preferred dehydrating agents and drying agents are the inorganic compounds.
- pigments examples include inorganic pigments such as titanium dioxide, iron oxides, zinc oxide, zinc phosphate, graphite and carbon black; organic pigments such as phthalocyanine compounds and azo pigments.
- extenders and fillers are minerals such as dolomite, plastorite, calcite, quartz, barite, magnesite, aragonite, silica, wollastonite, talc, chlorite, mica, kaolin and feldspar; synthetic inorganic compounds such as calcium carbonate, magnesium carbonate, barium sulphate, calcium silicate and silica; polymeric and inorganic microspheres such as uncoated or coated hollow and solid glass beads, uncoated or coated hollow and solid ceramic beads, porous and compact beads of polymeric materials such as poly(methyl methacrylate), poly(methyl methacrylate-co-ethylene glycol dimethacrylate), poly(styrene-co-ethylene glycol dimethacrylate), poly(styrene-co-divinylbenzene), polystyrene, poly(vinyl chloride).
- additives that can be added to an antifouling coating composition are reinforcing agents, thixotropic agents, thickening agents, anti-settling agents, plasticizers and solvents.
- Fibres include natural and synthetic inorganic fibres such as silicon-containing fibres, carbon fibres, oxide fibres, carbide fibres, nitride fibres, sulphide fibres, phosphate fibres, mineral fibres; metallic fibres; natural and synthetic organic fibres such as cellulose fibres, rubber fibres, acrylic fibres, polyamide fibres, polyimide, polyester fibres, polyhydrazide fibres, polyvinylchloride fibres, polyethylene fibres and others as described in WO 00/77102 .
- the fibres have an average length of 25 to 2,000 ⁇ m and an average thickness of 1 to 50 ⁇ m with a ratio between the average length and the average thickness of at least 5.
- thixotropic agents examples include silicas such as fumed silicas, organo-modified clays, amide waxes, polyamide waxes, amide derivatives, polyethylene waxes, oxidised polyethylene waxes, hydrogenated castor oil wax, ethyl cellulose, aluminium stearates and mixtures of thereof.
- plasticizers are chlorinated paraffins, phthalates, phosphate esters, sulphonamides, adipates and epoxidised vegetable oils.
- any of these optional components can be present in an amount ranging from 0.1 to 50 wt%, typically 0.5 to 20 wt%, preferably 0.75 to 15 wt% of the antifouling composition. It will be appreciated that the amount of these optional components will vary depending on the end use
- the antifouling composition contains a solvent.
- organic solvents and thinners are aromatic hydrocarbons such as xylene, toluene, mesitylene; ketones methyl ethyl ketone, methyl isobutyl ketone, methyl isoamyl ketone, cyclopentanone, cyclohexanone; esters such as butyl acetate, tert-butyl acetate, amyl acetate, isoamyl acetate, ethylene glycol methyl ether acetate; ethers such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dibutyl ether, dioxane, tetrahydrofuran, alcohols such as n-butanol, isobutanol, benzyl alcohol; ether
- Preferred solvents are aromatic solvents, especially xylene and mixtures of aromatic hydrocarbons.
- the amount of solvent is preferably as low as possible but is preferably sufficient to dissolve the at least one polyoxalate.
- the solvent content may be up to 50 wt% of the composition, preferably up to 45 wt% of the composition, such as up to 40 wt% but may be as low as 15 wt% or less, e.g. 10 wt% or less. Again, the skilled man will appreciate that the solvent content will vary depending on the other components present and the end use of the coating composition.
- the coating can be dispersed in an organic non-solvent for the film-forming components in the coating composition or in an aqueous dispersion.
- the antifouling coating composition of the invention can be applied to a whole or part of any object surface which is subject to fouling.
- the surface may be permanently or intermittantly underwater (e.g. through tide movement, different cargo loading or swell).
- the object surface will typically be the hull of a vessel or surface of a fixed marine object such as an oil platform or buoy.
- Application of the coating composition can be accomplished by any convenient means, e.g. via painting (e.g. with brush or roller) or spraying the coating onto the object.
- the surface will need to be separated from the seawater to allow coating.
- the application of the coating can be achieved as conventionally known in the art.
- the viscosity of the polymers are determined in accordance with ASTM D2196 using a Brookfield DV-I viscometer with LV-2 or LV-4 spindle at 12 rpm.
- the polymers are temperated to 23.0°C ⁇ 0.5°C before the measurements.
- the solids content in the polymer solutions are determined in accordance with ISO 3251.
- a test sample of 0.6 g ⁇ 0.1 g are taken out and dried in a ventilated oven at 150°C for 30 minutes.
- the weight of the residual material is considered to be the non-volatile matter (NVM).
- the non-volatile matter content is expressed in weight percent. The value given is the average of three parallels.
- the polymers are characterised by Gel Permeation Chromatography (GPC) measurement.
- GPC Gel Permeation Chromatography
- MFD molecular weight distribution
- PL-GPC 50 instrument with two PLgel 5 ⁇ m Mixed-D columns from Polymer Laboratories in series, tetrahydrofuran (THF) as eluent at ambient temperature and at a constant flow rate of 1 mL/min and with a refractive index (RI) detector.
- THF tetrahydrofuran
- RI refractive index
- the columns were calibrated using polystyrene standards Easivials PS-H from Polymer Laboratories.
- the data were processed using Cirrus software from Polymer Labs.
- Samples were prepared by dissolving an amount of polymer solution corresponding to 25 mg dry polymer in 5 mL THF. The samples were kept for minimum 3 hours at room temperature prior to sampling for the GPC measurements.
- the weight-average molecular weight (Mw), the number-average molecular weight (Mn) and the polydispersity index (PDI), given as Mw/Mn, are reported in the tables..
- the glass transition temperature (Tg) is obtained by Differential Scanning Calorimetry (DSC) measurements.
- DSC Differential Scanning Calorimetry
- the DSC measurements were performed on a TA Instruments DSC Q200. Samples were prepared by transfering a small amount of polymer solution to an aluminium pan and dry the samples for minimum 10 h at 50°C and 1 h at 150°C The samples of approx. 10 mg dry polymer material were meassured in open aluminum pans and scans were recorded at a heating and cooling rate of 10°C/min with an empty pan as reference. The onset value of the glass transition of the second heating is reported as the Tg of the polymers.
- Example 1 General procedure for preparation of polyoxalates by transesterification in melt
- 100 g of starting materials comprising a mixture of 1.0 mole eq. of diethyl oxalate or a mixture of diethyl oxalate and a dicarboxylic acid ester, 1.0 mole eq. of one or more diols and 0.02 mole eq. of catalyst are charged into a 500 ml three-necked glass flask equipped with magnetic stirrer, thermometer, condenser and nitrogen inlet. The mixture is heated slowly under nitrogen to 190°C on a temperature controlled oil bath while the condensate is distilled.
- the heating rate is controlled so that the temperature in the outlet does not exceed the boiling point of the condensate..
- the temperature is maintained at 190°C until 80-90% of the theoretical amount of condensate is collected.
- the nitrogen inlet is closed and vacuum is applied.
- the vacuum is adjusted gradually down to 0.1 mbar.
- the temperature is maintained at 190°C for 2-4 hours.
- the polymer melt is cooled to approx. 100°C under vacuum.
- the vacuum is removed and solvent is added.
- the polymer solution is cooled to room temperature.
- the polyoxalates PO-1 to PO-4 in Table 1 are prepared according to this procedure.
- Table 1 Ingredients and properties of polyoxalate solutions PO-1 to PO-4 PO-1 PO-2 PO-3 PO-4 Dicarboxylic acid esters Diethyl oxalate 54.06 50.13 50.09 30.14 Dimethyl isophthalate - - - 21.56 Diols 1,4-Cyclohexanedimethanol 26.67 21.27 14.83 22.88 Neopentyl glycol 19.26 - - - Reactor charge (g) 2,2,4-Trimethyl-1,3-pentanediol - 28.59 35.08 - 2-Butyl-2-ethyl-1,3-propanediol - - - 25.42 1,6-Hexanediol - - - - Catalyst Dibutyltin oxide 0.0376 0.0349 0.0348 0.0322 Thinning (g) Solvent Xy
- 250 g of starting materials comprising a mixture of 1.0 mole eq. of diethyl oxalate or a mixture of diethyl oxalate and a dicarboxylic acid ester, 1.05 mole eq. of one or more diols and 0.02 mole eq. of catalyst are charged into a 250 ml temperature controlled reactor vessel equipped with mechanical stirrer, thermometer, condenser and nitrogen inlet. The mixture is heated slowly under nitrogen to 190°C while the condensate is distilled. The heating rate is controlled so that the temperature in the outlet does not exceed the boiling point of the condensate. The pre-polymerisation reaction is run until 80-90% of the theoretical amount of condensate is collected.
- the nitrogen inlet is closed and vacuum is applied.
- the vacuum is adjusted gradually down to 100 mbar.
- the temperature and vacuum is maintained for 3 hours.
- the polymer melt is cooled to approx. 100°C under vacuum.
- the vacuum is removed and solvent is added.
- the polymer solution is cooled to room temperature.
- the polyoxalates PO-5 to PO-19 in Table 2 are prepared according to this procedure.
- the obtained polyoxalate had Mw of 2,800, PDI of 1.9.
- the ingredients are mixed and ground to a fineness of ⁇ 30 ⁇ m using a highspeed disperser. Any ingredients sensitive to the high shear forces and temperature in the grinding process are added in the let-down.
- the compositions of the prepared coating compositions are presented in Table 3 and Table 4. Any curing agent and accelerator are mixed with the coating composition just before use.
- the high-shear viscosity of the antifouling coating composition is determined in accordance with ASTM D4287 using a cone-plate viscometer.
- the volatile organic compound (VOC) content of the antifouling coating composition is calculated in accordance with ASTM D5201.
- the polishing rate is determined by measuring the reduction in film thickness of a coating film over time.
- PVC disc are used.
- the coating compositions are applied as radial stripes on the disc using a film applicator.
- the thickness of the dry coating films are measured by means of a suitable electronic film thickness gauge.
- the PVC discs are mounted on a shaft and rotated in a container in which seawater is flowing through. Natural seawater which has been filtered and temperature-adjusted to 25°C ⁇ 2°C is used.
- the PVC discs are taken out at regular intervals for measuring the film thickness.
- the discs are rinsed and allowed to dry overnight at room temperature before measuring the film thickness.
- Table 3 Ingredients in parts by weight of physically drying coating compositions C-1 to C-3 C-1 C-2 C-3 Binder Polyoxalate solution PO-1 PO-3 PO-4 30.68 31.85 30.63 Biocides Cuprous oxide 36.72 36.71 36.72 Copper pyrithione 1.35 1.35 1.35 Pigments Iron oxide red 1.21 1.21 Titanium dioxide 1.18 1.18 1.18 Extenders Zinc oxide red seal 0.97 0.97 0.97 Barium sulfate 9.57 9.57 9.57 9.57 Nepheline syenite 2.95 2.95 2.95 Dehydrating agent Calcium sulfate 1.36 1.36 1.36 Thixotropic agents Disparlon A603-20X (1) 1.92 1.92 1.92 Disparlon 4401-25X (2) 0.88 0.88 0.88 Solvents Xylene 5.46 4.30 5.51 Solvesso 100 5.75 5.75 5.75 Coating properties Viscosity (cP) 620 200 260 Calculated VOC (g/L) 450 450 450 Polishing rate ( ⁇ m/month)
- Disparlon 4401-25X is a polyethylene wax, 25% in xylene; produced by Kusumoto Chemicals, Ltd.
- Table 4 Ingredients in parts by weight of 2-component curable coating compositions C-4 to C-9 C-4 C-5 C-6 C-7 C-8 C-9 Binder Polyoxalate solution PO-5 PO-6 PO-7 PO-8 PO-9 PO-1 27.57 26.43 27.67 26.38 26.39 26.40 Biocides Cuprous oxide 39.63 39.62 39.77 39.75 39.63 39.74 Copper pyrithione 1.59 1.60 1.61 1.61 1.59 1.61 Pigments Iron oxide red 1.96 1.97 1.98 1.98 1.96 1.98 Titanium dioxide 1.00 1.00 1.00 1.00 1.00 1.00 Extenders Barium sulfate 7.44 7.44 7.46 7.46 7.44 7.46 Magnesium carbonate 5.18 5.18 5.20 5.19 5.17 5.19 Nepheline syenite 2.83 2.84 2.85 2.85 2.82 2.85 Dehydrating agents Calcium sulfate 1.
- Disparlon A603-20X is an amide wax, 20% in xylene; produced by Kusumoto Chemicals, Ltd.
- Disparlon 4401-25X is a polyethylene wax, 25% in xylene; produced by Kusumoto Chemicals, Ltd.
- Desmodur N 75 BA is an aliphatic polyisocyanate resin based on hexamethylene diisocyanate (HDI), 75% in butyl acetate; produced by Bayer MaterialScience AG.
- the polishing rate of the reference paint was 2.3 ⁇ m/month when tested in parallel with the coatings in Table 3 and Table 4.
- the reference paint is SeaQuantum Classic light red from Jotun AS, which is a high performance self-polishing antifouling coating, based on a hydrolysing organosilyl polymer as binder.
- the data shows that an antifouling system comprising a polyoxalate binder is self-polishing.
- the self-polishing allows a controlled leaching of biocide that would keep a surface free of marine organisms.
- Our results show that the polyoxalate binder of this invention polishes faster than a reference commercial silyl ester copolymer binder containing fouling composition.
- a faster polishing system may be advantageously utilised on stationary installations or vessels that move slowly (e.g. less than 10 knots) and/or that operate in cold water (e.g. less than 10°C) since the hydrolysis rate is dependent on temperature.
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Claims (15)
- Antifouling-Beschichtungszusammensetzung, die mindestens ein Polyoxalat und mindestens ein biologisch aktives Mittel umfasst, welches die Ansiedlung mariner Organismen auf einer Oberfläche verhindert und/oder die Entfernung mariner Organismen von einer Oberfläche unterstützt.
- Antifouling-Beschichtungszusammensetzung gemäß Anspruch 1, dadurch gekennzeichnet, dass das Polyoxalat Polykondensationsreaktionsprodukte aus Oxalsäure oder einem Derivat davon mit mindestens einem Diol, vorzugsweise einem gesättigten und aliphatischen Diol, umfasst.
- Antifouling-Beschichtungszusammensetzung gemäß Anspruch 2, dadurch gekennzeichnet, dass das molare Verhältnis zwischen der Oxalsäure oder dem Derivat davon und dem Diol in der Polykondensationsreaktion kleiner als 2,0 und größer als 0,5, noch bevorzugter nicht oberhalb von 1,0 ist.
- Antifouling-Beschichtungszusammensetzung gemäß einem der Ansprüche 2 - 3, dadurch gekennzeichnet, dass die Oxalsäure oder das Derivat davon ein Dialkyloxalat, noch bevorzugter Dimethyloxalat oder Diethyloxalat, ist.
- Antifouling-Beschichtungszusammensetzung gemäß einem der Ansprüche 2 - 4, dadurch gekennzeichnet, dass die aromatischen Diole 50 Mol-% oder weniger der Gesamtmenge der Diole umfassen, die in der Polykondensationsreaktion eingesetzt werden, noch bevorzugter nicht mehr als 30 Mol-%, am meisten bevorzugt nicht mehr als 10 Mol-%, oder die ungesättigten aliphatischen Diole 10 Mol-% oder weniger der Gesamtmenge der Diole umfassen, die in der Polykondensationsreaktion eingesetzt werden.
- Antifouling-Beschichtungszusammensetzung gemäß einem der Ansprüche 2 - 5, dadurch gekennzeichnet, dass das Polyoxalat sich wiederholende Einheiten umfasst, die von Polyolen mit mehr als zwei Hydroxylgruppen abgeleitet sind, vorzugsweise wobei Polyole 10 Mol-% oder weniger der Gesamtmenge der Diole und Polyole bilden, die in der Polykondensationsreaktion vorliegen.
- Antifouling-Beschichtungszusammensetzung gemäß einem der Ansprüche 2 - 6, dadurch gekennzeichnet, dass das Polyoxalat eine oder mehr Einheiten umfasst, die durch die Polykondensationsreaktion eines Diamins, einer Dicarbonsäure oder Derivaten davon oder von hydroxyfunktionellen Carbonsäuren oder Derivaten davon erhalten wurden.
- Antifouling-Beschichtungszusammensetzung gemäß einem der Ansprüche 1 - 7, dadurch gekennzeichnet, dass das Polyoxalat ein Gewichtsmittel der Molekülmasse (Mw) von 1.000 bis 40.000 aufweist und/oder amorph ist.
- Antifouling-Beschichtungszusammensetzung gemäß einem der Ansprüche 1 - 8, die ein oder mehrere Lösemittel, z. B. Xylol, und/oder ein oder mehrere Zusätze umfassen, die ausgewählt sind aus biologisch aktiven Verbindungen, anderen Bindemitteln, Weichmachern, Pigmenten, Streckmitteln, Füllstoffen, wasserentziehenden Mitteln, Trockenmitteln, Härtungsmitteln, thixotropen Mitteln, Verdickungsmitteln, Absetzverhinderungsmitteln, Verstärkungsmitteln, Verdünnungsmitteln und zusätzlichen Lösemitteln.
- Antifouling-Beschichtungszusammensetzung gemäß einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, dass es eine physikalisch trocknende Beschichtungszusammensetzung oder eine härtende Beschichtungszusammensetzung ist.
- Antifouling-Beschichtungszusammensetzung gemäß den Ansprüchen 1 bis 10, dadurch gekennzeichnet, dass das Polyoxalat hydroxyfunktionelle Endgruppen aufweist und die Zusammensetzung ein Härtungsmittel umfasst, welches ausgewählt ist aus Isocyanaten, polymeren Isocyanaten und Isocyanat-Prepolymeren; oder dadurch gekennzeichnet, dass das Bindemittel epoxyfunktionelle Endgruppen aufweist und das Härtungsmittel ausgewählt ist aus Aminen und Polyaminen.
- Antifouling-Beschichtungszusammensetzung gemäß einem der Ansprüche 1 bis 11, gekennzeichnet durch einen Gehalt an Feststoffen von nicht weniger als 50 Gew.-%, und/oder einen Gehalt flüchtiger organischer Verbindungen (VOC) unterhalb von 400 g/L.
- Kit, das (I) eine Antifouling-Beschichtungszusammensetzung, die mindestens ein Polyoxalat und mindestens ein biologisch aktives Mittel aufweist, welches die Ansiedlung mariner Organismen auf einer Oberfläche verhindert und/oder die Entfernung mariner Organismen von einer Oberfläche unterstützt und (II) mindestens ein Härtungsmittel umfasst.
- Verwendung von mindestens einem Polyoxalat als Bindemittel in einer Antifouling-Beschichtungszusammensetzung, wobei die Antifouling-Beschichtungszusammensetzung ein biologisch aktives Mittel aufweist, welches die Ansiedlung von marinen Organismen auf einer Oberfläche verhindert und/oder die Entfernung mariner Organismen von einer Oberfläche unterstützt.
- Gegenstand, beschichtet mit einer Antifouling-Beschichtung gemäß einem der Ansprüche 1 bis 12.
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EP2348077B1 (de) | 2010-01-26 | 2013-04-03 | Jotun A/S | Fäulnisverhindernde Zusammensetzung |
CN103228744B (zh) | 2010-10-14 | 2016-10-12 | 汉伯公司 | 高固含量防污油漆组合物 |
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EP2726560B1 (de) * | 2011-06-30 | 2017-03-01 | Hempel A/S | Fäulnisverhindernde anstrichfarbenzusammensetzung mit hohem feststoffgehalt |
DE202012100443U1 (de) * | 2012-02-09 | 2012-02-28 | Wenko-Wenselaar Gmbh & Co. Kg | Duschvorhang mit Antibewuchs-Ausrüstung |
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CN103694879A (zh) * | 2013-12-13 | 2014-04-02 | 青岛海洋新材料科技有限公司 | 一种可降解防污涂料 |
EP2902452A1 (de) * | 2014-01-31 | 2015-08-05 | Jotun A/S | Fäulnisverhindernde Zusammensetzung |
EP2902453A1 (de) * | 2014-01-31 | 2015-08-05 | Jotun A/S | Fäulnisverhindernde Zusammensetzung |
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US9546283B2 (en) | 2017-01-17 |
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KR20100136457A (ko) | 2010-12-28 |
CN101970529A (zh) | 2011-02-09 |
EP2247642A1 (de) | 2010-11-10 |
ES2436528T3 (es) | 2014-01-02 |
PL2247642T3 (pl) | 2014-01-31 |
JP5706692B2 (ja) | 2015-04-22 |
KR101630649B1 (ko) | 2016-06-15 |
JP2011511871A (ja) | 2011-04-14 |
CN101970529B (zh) | 2014-02-19 |
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